TWI509030B - 偶氮化合物、染料系偏光膜及偏光板 - Google Patents

偶氮化合物、染料系偏光膜及偏光板 Download PDF

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Publication number: TWI509030B
Authority: TW; Taiwan
Prior art keywords: group; sulfonic acid; dye; salt; azo compound
Prior art date: 2011-02-07

Application number

TW101103856A

Other languages

English (en)

Chinese (zh)

Other versions

TW201241096A (en

Inventor

Takahiro Higeta

Takuto Nishiguchi

Original Assignee

Nippon Kayaku Kk

Polatechno Co Ltd

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

2011-02-07

Filing date

2012-02-07

Publication date

2015-11-21

2012-02-07 Application filed by Nippon Kayaku Kk, Polatechno Co Ltd filed Critical Nippon Kayaku Kk

2012-10-16 Publication of TW201241096A publication Critical patent/TW201241096A/zh

2015-11-21 Application granted granted Critical

2015-11-21 Publication of TWI509030B publication Critical patent/TWI509030B/zh

Links

-1 Azo compound Chemical class 0.000 title claims description 118
230000010287 polarization Effects 0.000 title description 21
125000001424 substituent group Chemical group 0.000 claims description 90
239000000975 dye Substances 0.000 claims description 87
125000003277 amino group Chemical group 0.000 claims description 66
125000000542 sulfonic acid group Chemical group 0.000 claims description 66
125000003545 alkoxy group Chemical group 0.000 claims description 65
239000004973 liquid crystal related substance Substances 0.000 claims description 56
150000003839 salts Chemical class 0.000 claims description 54
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 39
125000004432 carbon atom Chemical group C* 0.000 claims description 34
125000000217 alkyl group Chemical group 0.000 claims description 31
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 29
125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 28
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 28
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 25
YTZPUTADNGREHA-UHFFFAOYSA-N 2h-benzo[e]benzotriazole Chemical group C1=CC2=CC=CC=C2C2=NNN=C21 YTZPUTADNGREHA-UHFFFAOYSA-N 0.000 claims description 19
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 18
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 18
239000004372 Polyvinyl alcohol Substances 0.000 claims description 17
229920002451 polyvinyl alcohol Polymers 0.000 claims description 17
125000000751 azo group Chemical group [*]N=N[*] 0.000 claims description 14
230000001681 protective effect Effects 0.000 claims description 10
229920005989 resin Polymers 0.000 claims description 9
239000011347 resin Substances 0.000 claims description 9
238000004519 manufacturing process Methods 0.000 claims description 8
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 5
239000000463 material Substances 0.000 claims description 4
IMROMDMJAWUWLK-UHFFFAOYSA-N Ethenol Chemical compound OC=C IMROMDMJAWUWLK-UHFFFAOYSA-N 0.000 claims description 3
229920006026 co-polymeric resin Polymers 0.000 claims description 2
125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 claims description 2
150000001875 compounds Chemical class 0.000 description 78
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 36
238000010521 absorption reaction Methods 0.000 description 35
238000002834 transmittance Methods 0.000 description 34
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 26
239000000243 solution Substances 0.000 description 24
VOWZNBNDMFLQGM-UHFFFAOYSA-N 2,5-dimethylaniline Chemical compound CC1=CC=C(C)C(N)=C1 VOWZNBNDMFLQGM-UHFFFAOYSA-N 0.000 description 22
239000000758 substrate Substances 0.000 description 22
239000007822 coupling agent Substances 0.000 description 21
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 21
PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 20
238000005859 coupling reaction Methods 0.000 description 19
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 18
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 18
LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 18
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 17
239000002253 acid Substances 0.000 description 17
239000010410 layer Substances 0.000 description 17
238000003756 stirring Methods 0.000 description 14
229920006254 polymer film Polymers 0.000 description 13
238000000034 method Methods 0.000 description 12
230000000052 comparative effect Effects 0.000 description 11
238000006193 diazotization reaction Methods 0.000 description 11
230000007935 neutral effect Effects 0.000 description 11
230000008878 coupling Effects 0.000 description 10
238000010168 coupling process Methods 0.000 description 10
210000002858 crystal cell Anatomy 0.000 description 10
239000007864 aqueous solution Substances 0.000 description 9
239000003086 colorant Substances 0.000 description 9
239000011521 glass Substances 0.000 description 9
235000010288 sodium nitrite Nutrition 0.000 description 9
KJCVRFUGPWSIIH-UHFFFAOYSA-N 1-naphthol Chemical compound C1=CC=C2C(O)=CC=CC2=C1 KJCVRFUGPWSIIH-UHFFFAOYSA-N 0.000 description 8
JJYPMNFTHPTTDI-UHFFFAOYSA-N 3-methylaniline Chemical compound CC1=CC=CC(N)=C1 JJYPMNFTHPTTDI-UHFFFAOYSA-N 0.000 description 8
239000002585 base Substances 0.000 description 8
238000004043 dyeing Methods 0.000 description 8
238000001914 filtration Methods 0.000 description 8
239000000203 mixture Substances 0.000 description 8
229910000029 sodium carbonate Inorganic materials 0.000 description 8
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 7
239000011630 iodine Substances 0.000 description 7
229910052740 iodine Inorganic materials 0.000 description 7
239000011241 protective layer Substances 0.000 description 7
238000006467 substitution reaction Methods 0.000 description 7
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical group OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 6
239000007767 bonding agent Substances 0.000 description 6
KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 6
239000004327 boric acid Substances 0.000 description 6
XPVVBMXZTSOIQD-UHFFFAOYSA-N 3-(2-amino-4-methylphenoxy)propane-1-sulfonic acid Chemical compound CC1=CC=C(OCCCS(O)(=O)=O)C(N)=C1 XPVVBMXZTSOIQD-UHFFFAOYSA-N 0.000 description 5
239000000853 adhesive Substances 0.000 description 5
230000001070 adhesive effect Effects 0.000 description 5
238000007796 conventional method Methods 0.000 description 5
125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 5
230000003287 optical effect Effects 0.000 description 5
WXWCDTXEKCVRRO-UHFFFAOYSA-N para-Cresidine Chemical compound COC1=CC=C(C)C=C1N WXWCDTXEKCVRRO-UHFFFAOYSA-N 0.000 description 5
238000005185 salting out Methods 0.000 description 5
ILJSQTXMGCGYMG-UHFFFAOYSA-N triacetic acid Chemical compound CC(=O)CC(=O)CC(O)=O ILJSQTXMGCGYMG-UHFFFAOYSA-N 0.000 description 5
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 4
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
150000001412 amines Chemical class 0.000 description 4
150000001448 anilines Chemical class 0.000 description 4
150000004982 aromatic amines Chemical class 0.000 description 4
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 4
230000008859 change Effects 0.000 description 4
NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 3
IMUUNYPYNWXUBO-UHFFFAOYSA-N 4-aminobenzene-1,3-disulfonic acid Chemical compound NC1=CC=C(S(O)(=O)=O)C=C1S(O)(=O)=O IMUUNYPYNWXUBO-UHFFFAOYSA-N 0.000 description 3
STOOUUMSJPLRNI-UHFFFAOYSA-N 5-amino-4-hydroxy-3-[[4-[4-[(4-hydroxyphenyl)diazenyl]phenyl]phenyl]diazenyl]-6-[(4-nitrophenyl)diazenyl]naphthalene-2,7-disulfonic acid Chemical compound OS(=O)(=O)C1=CC2=CC(S(O)(=O)=O)=C(N=NC=3C=CC(=CC=3)C=3C=CC(=CC=3)N=NC=3C=CC(O)=CC=3)C(O)=C2C(N)=C1N=NC1=CC=C([N+]([O-])=O)C=C1 STOOUUMSJPLRNI-UHFFFAOYSA-N 0.000 description 3
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 3
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
229920002284 Cellulose triacetate Polymers 0.000 description 3
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
NNLVGZFZQQXQNW-ADJNRHBOSA-N [(2r,3r,4s,5r,6s)-4,5-diacetyloxy-3-[(2s,3r,4s,5r,6r)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxy-6-[(2r,3r,4s,5r,6s)-4,5,6-triacetyloxy-2-(acetyloxymethyl)oxan-3-yl]oxyoxan-2-yl]methyl acetate Chemical compound O([C@@H]1O[C@@H]([C@H]([C@H](OC(C)=O)[C@H]1OC(C)=O)O[C@H]1[C@@H]([C@@H](OC(C)=O)[C@H](OC(C)=O)[C@@H](COC(C)=O)O1)OC(C)=O)COC(=O)C)[C@@H]1[C@@H](COC(C)=O)O[C@@H](OC(C)=O)[C@H](OC(C)=O)[C@H]1OC(C)=O NNLVGZFZQQXQNW-ADJNRHBOSA-N 0.000 description 3
229910052799 carbon Inorganic materials 0.000 description 3
239000003795 chemical substances by application Substances 0.000 description 3
238000000576 coating method Methods 0.000 description 3
229920001577 copolymer Polymers 0.000 description 3
150000008049 diazo compounds Chemical class 0.000 description 3
239000001257 hydrogen Substances 0.000 description 3
229910052739 hydrogen Inorganic materials 0.000 description 3
239000003960 organic solvent Substances 0.000 description 3
239000000126 substance Substances 0.000 description 3
NAZDVUBIEPVUKE-UHFFFAOYSA-N 2,5-dimethoxyaniline Chemical compound COC1=CC=C(OC)C(N)=C1 NAZDVUBIEPVUKE-UHFFFAOYSA-N 0.000 description 2
UFFBMTHBGFGIHF-UHFFFAOYSA-N 2,6-dimethylaniline Chemical compound CC1=CC=CC(C)=C1N UFFBMTHBGFGIHF-UHFFFAOYSA-N 0.000 description 2
KZKGEEGADAWJFS-UHFFFAOYSA-N 2-amino-5-methoxybenzenesulfonic acid Chemical compound COC1=CC=C(N)C(S(O)(=O)=O)=C1 KZKGEEGADAWJFS-UHFFFAOYSA-N 0.000 description 2
FZZMTSNZRBFGGU-UHFFFAOYSA-N 2-chloro-7-fluoroquinazolin-4-amine Chemical compound FC1=CC=C2C(N)=NC(Cl)=NC2=C1 FZZMTSNZRBFGGU-UHFFFAOYSA-N 0.000 description 2
MLPVBIWIRCKMJV-UHFFFAOYSA-N 2-ethylaniline Chemical compound CCC1=CC=CC=C1N MLPVBIWIRCKMJV-UHFFFAOYSA-N 0.000 description 2
MKARNSWMMBGSHX-UHFFFAOYSA-N 3,5-dimethylaniline Chemical compound CC1=CC(C)=CC(N)=C1 MKARNSWMMBGSHX-UHFFFAOYSA-N 0.000 description 2
ZDIRCGKEOWZBIM-UHFFFAOYSA-N 4-amino-2-methylbenzenesulfonic acid Chemical compound CC1=CC(N)=CC=C1S(O)(=O)=O ZDIRCGKEOWZBIM-UHFFFAOYSA-N 0.000 description 2
HVBSAKJJOYLTQU-UHFFFAOYSA-N 4-aminobenzenesulfonic acid Chemical compound NC1=CC=C(S(O)(=O)=O)C=C1 HVBSAKJJOYLTQU-UHFFFAOYSA-N 0.000 description 2
HQWKOJIWYQRIAT-UHFFFAOYSA-N 6-anilinonaphthalen-1-ol Chemical compound C=1C=C2C(O)=CC=CC2=CC=1NC1=CC=CC=C1 HQWKOJIWYQRIAT-UHFFFAOYSA-N 0.000 description 2
IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 2
239000005711 Benzoic acid Substances 0.000 description 2
YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 2
IOVCWXUNBOPUCH-UHFFFAOYSA-M Nitrite anion Chemical compound [O-]N=O IOVCWXUNBOPUCH-UHFFFAOYSA-M 0.000 description 2
UFUQRRYHIHJMPB-DUCFOALUSA-L Sirius red 4B Chemical compound [Na+].[Na+].OS(=O)(=O)c1cc2cc(NC(=O)c3ccccc3)ccc2c([O-])c1\N=N\c1ccc(cc1)\N=N\c1ccc(cc1)S([O-])(=O)=O UFUQRRYHIHJMPB-DUCFOALUSA-L 0.000 description 2
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
235000010724 Wisteria floribunda Nutrition 0.000 description 2
238000010306 acid treatment Methods 0.000 description 2
230000002378 acidificating effect Effects 0.000 description 2
229910052783 alkali metal Inorganic materials 0.000 description 2
125000003806 alkyl carbonyl amino group Chemical group 0.000 description 2
150000003863 ammonium salts Chemical class 0.000 description 2
235000010233 benzoic acid Nutrition 0.000 description 2
239000004568 cement Substances 0.000 description 2
238000006243 chemical reaction Methods 0.000 description 2
230000006866 deterioration Effects 0.000 description 2
239000012954 diazonium Substances 0.000 description 2
238000002845 discoloration Methods 0.000 description 2
125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 2
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
239000011737 fluorine Substances 0.000 description 2
229910052731 fluorine Inorganic materials 0.000 description 2
229910052500 inorganic mineral Inorganic materials 0.000 description 2
230000007774 longterm Effects 0.000 description 2
QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 2
229910052753 mercury Inorganic materials 0.000 description 2
229910001507 metal halide Inorganic materials 0.000 description 2
150000005309 metal halides Chemical class 0.000 description 2
239000011707 mineral Substances 0.000 description 2
238000002156 mixing Methods 0.000 description 2
150000004780 naphthols Chemical class 0.000 description 2
RNVCVTLRINQCPJ-UHFFFAOYSA-N o-toluidine Chemical compound CC1=CC=CC=C1N RNVCVTLRINQCPJ-UHFFFAOYSA-N 0.000 description 2
230000009467 reduction Effects 0.000 description 2
238000000926 separation method Methods 0.000 description 2
239000011780 sodium chloride Substances 0.000 description 2
159000000000 sodium salts Chemical class 0.000 description 2
229950000244 sulfanilic acid Drugs 0.000 description 2
239000000725 suspension Substances 0.000 description 2
NAWXUBYGYWOOIX-SFHVURJKSA-N (2s)-2-[[4-[2-(2,4-diaminoquinazolin-6-yl)ethyl]benzoyl]amino]-4-methylidenepentanedioic acid Chemical compound C1=CC2=NC(N)=NC(N)=C2C=C1CCC1=CC=C(C(=O)N[C@@H](CC(=C)C(O)=O)C(O)=O)C=C1 NAWXUBYGYWOOIX-SFHVURJKSA-N 0.000 description 1
VBUBGTCJRMYYRA-UHFFFAOYSA-N 2,5-diethylaniline Chemical compound CCC1=CC=C(CC)C(N)=C1 VBUBGTCJRMYYRA-UHFFFAOYSA-N 0.000 description 1
SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 1
LTPSRQRIPCVMKQ-UHFFFAOYSA-N 2-amino-5-methylbenzenesulfonic acid Chemical compound CC1=CC=C(N)C(S(O)(=O)=O)=C1 LTPSRQRIPCVMKQ-UHFFFAOYSA-N 0.000 description 1
LTASFWDWBYFZQQ-UHFFFAOYSA-N 2-amino-5-nitrobenzenesulfonic acid Chemical compound NC1=CC=C([N+]([O-])=O)C=C1S(O)(=O)=O LTASFWDWBYFZQQ-UHFFFAOYSA-N 0.000 description 1
LDCCBULMAFILCT-UHFFFAOYSA-N 2-aminobenzene-1,4-disulfonic acid Chemical compound NC1=CC(S(O)(=O)=O)=CC=C1S(O)(=O)=O LDCCBULMAFILCT-UHFFFAOYSA-N 0.000 description 1
ZMCHBSMFKQYNKA-UHFFFAOYSA-M 2-aminobenzenesulfonate Chemical compound NC1=CC=CC=C1S([O-])(=O)=O ZMCHBSMFKQYNKA-UHFFFAOYSA-M 0.000 description 1
WNRGWPVJGDABME-UHFFFAOYSA-N 3,5-Dimethoxyaniline Chemical compound COC1=CC(N)=CC(OC)=C1 WNRGWPVJGDABME-UHFFFAOYSA-N 0.000 description 1
HQUSCQMXYRCTQZ-UHFFFAOYSA-N 3-(2-amino-4-methylphenoxy)butane-1-sulfonic acid Chemical compound OS(=O)(=O)CCC(C)OC1=CC=C(C)C=C1N HQUSCQMXYRCTQZ-UHFFFAOYSA-N 0.000 description 1
FLIOATBXVNLPLK-UHFFFAOYSA-N 3-amino-4-methoxybenzenesulfonic acid Chemical compound COC1=CC=C(S(O)(=O)=O)C=C1N FLIOATBXVNLPLK-UHFFFAOYSA-N 0.000 description 1
ZAJAQTYSTDTMCU-UHFFFAOYSA-N 3-aminobenzenesulfonic acid Chemical compound NC1=CC=CC(S(O)(=O)=O)=C1 ZAJAQTYSTDTMCU-UHFFFAOYSA-N 0.000 description 1
AMKPQMFZCBTTAT-UHFFFAOYSA-N 3-ethylaniline Chemical compound CCC1=CC=CC(N)=C1 AMKPQMFZCBTTAT-UHFFFAOYSA-N 0.000 description 1
125000004207 3-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(OC([H])([H])[H])=C1[H] 0.000 description 1
ALYNCZNDIQEVRV-PZFLKRBQSA-N 4-amino-3,5-ditritiobenzoic acid Chemical compound [3H]c1cc(cc([3H])c1N)C(O)=O ALYNCZNDIQEVRV-PZFLKRBQSA-N 0.000 description 1
HKWPUUYEGGDLJF-UHFFFAOYSA-N 4-hydroxynaphthalene-2-sulfonic acid Chemical compound C1=CC=C2C(O)=CC(S(O)(=O)=O)=CC2=C1 HKWPUUYEGGDLJF-UHFFFAOYSA-N 0.000 description 1
PHRVJZNHPVJYOM-UHFFFAOYSA-N 5-acetamido-2-aminobenzenesulfonic acid Chemical compound CC(=O)NC1=CC=C(N)C(S(O)(=O)=O)=C1 PHRVJZNHPVJYOM-UHFFFAOYSA-N 0.000 description 1
KBZFDRWPMZESDI-UHFFFAOYSA-N 5-aminobenzene-1,3-dicarboxylic acid Chemical compound NC1=CC(C(O)=O)=CC(C(O)=O)=C1 KBZFDRWPMZESDI-UHFFFAOYSA-N 0.000 description 1
XLTYSVRHUHRGAL-UHFFFAOYSA-N CC1=CC(=C(C=C1)OC)N=NC2=C(C=CC(=C2)O)N(N=NC3=CC=C(C=C3)N)N=NC4=C(C=CC(=C4)OC)OC Chemical compound CC1=CC(=C(C=C1)OC)N=NC2=C(C=CC(=C2)O)N(N=NC3=CC=C(C=C3)N)N=NC4=C(C=CC(=C4)OC)OC XLTYSVRHUHRGAL-UHFFFAOYSA-N 0.000 description 1
JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 1
CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 1
AFBPFSWMIHJQDM-UHFFFAOYSA-N N-methylaniline Chemical compound CNC1=CC=CC=C1 AFBPFSWMIHJQDM-UHFFFAOYSA-N 0.000 description 1
GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 1
XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 1
DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 1
150000001241 acetals Chemical class 0.000 description 1
238000003916 acid precipitation Methods 0.000 description 1
150000001298 alcohols Chemical class 0.000 description 1
150000001336 alkenes Chemical class 0.000 description 1
230000029936 alkylation Effects 0.000 description 1
238000005804 alkylation reaction Methods 0.000 description 1
RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical class COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 1
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
239000000987 azo dye Substances 0.000 description 1
125000003943 azolyl group Chemical group 0.000 description 1
PXXJHWLDUBFPOL-UHFFFAOYSA-N benzamidine Chemical group NC(=N)C1=CC=CC=C1 PXXJHWLDUBFPOL-UHFFFAOYSA-N 0.000 description 1
SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 1
229940092714 benzenesulfonic acid Drugs 0.000 description 1
239000011230 binding agent Substances 0.000 description 1
230000000903 blocking effect Effects 0.000 description 1
239000005388 borosilicate glass Substances 0.000 description 1
125000004106 butoxy group Chemical group [*]OC([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
229920006317 cationic polymer Polymers 0.000 description 1
229920002301 cellulose acetate Polymers 0.000 description 1
229910000420 cerium oxide Inorganic materials 0.000 description 1
239000011248 coating agent Substances 0.000 description 1
238000004040 coloring Methods 0.000 description 1
239000000470 constituent Substances 0.000 description 1
238000007334 copolymerization reaction Methods 0.000 description 1
LDHQCZJRKDOVOX-NSCUHMNNSA-N crotonic acid Chemical compound C\C=C\C(O)=O LDHQCZJRKDOVOX-NSCUHMNNSA-N 0.000 description 1
150000001925 cycloalkenes Chemical class 0.000 description 1
238000007033 dehydrochlorination reaction Methods 0.000 description 1
150000001989 diazonium salts Chemical class 0.000 description 1
IJGRMHOSHXDMSA-UHFFFAOYSA-O diazynium Chemical compound [NH+]#N IJGRMHOSHXDMSA-UHFFFAOYSA-O 0.000 description 1
PBOIUUROGJVVNC-UHFFFAOYSA-L disodium 2-hydroxy-5-[[4-[[2-methoxy-4-[(3-sulfonatophenyl)diazenyl]phenyl]carbamoylamino]phenyl]diazenyl]benzoate Chemical compound [Na+].[Na+].COc1cc(ccc1NC(=O)Nc1ccc(cc1)N=Nc1ccc(O)c(c1)C([O-])=O)N=Nc1cccc(c1)S([O-])(=O)=O PBOIUUROGJVVNC-UHFFFAOYSA-L 0.000 description 1
OYUZMQYZGSMPII-UHFFFAOYSA-L disodium 4-hydroxy-7-[(5-hydroxy-6-phenyldiazenyl-7-sulfonatonaphthalen-2-yl)amino]-3-phenyldiazenylnaphthalene-2-sulfonate Chemical compound [Na+].[Na+].Oc1c(N=Nc2ccccc2)c(cc2cc(Nc3ccc4c(O)c(N=Nc5ccccc5)c(cc4c3)S([O-])(=O)=O)ccc12)S([O-])(=O)=O OYUZMQYZGSMPII-UHFFFAOYSA-L 0.000 description 1
DSARWKALPGYFTA-UHFFFAOYSA-L disodium 4-hydroxy-7-[(5-hydroxy-6-phenyldiazenyl-7-sulfonatonaphthalen-2-yl)carbamoylamino]-3-phenyldiazenylnaphthalene-2-sulfonate Chemical compound [Na+].[Na+].[O-]S(=O)(=O)C1=CC2=CC(NC(=O)NC=3C=C4C=C(C(N=NC=5C=CC=CC=5)=C(O)C4=CC=3)S([O-])(=O)=O)=CC=C2C(O)=C1N=NC1=CC=CC=C1 DSARWKALPGYFTA-UHFFFAOYSA-L 0.000 description 1
230000000694 effects Effects 0.000 description 1
239000000839 emulsion Substances 0.000 description 1
125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 description 1
238000011156 evaluation Methods 0.000 description 1
HCDGVLDPFQMKDK-UHFFFAOYSA-N hexafluoropropylene Chemical group FC(F)=C(F)C(F)(F)F HCDGVLDPFQMKDK-UHFFFAOYSA-N 0.000 description 1
238000005470 impregnation Methods 0.000 description 1
230000006872 improvement Effects 0.000 description 1
238000002347 injection Methods 0.000 description 1
239000007924 injection Substances 0.000 description 1
PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
239000012948 isocyanate Substances 0.000 description 1
150000002576 ketones Chemical class 0.000 description 1
238000010030 laminating Methods 0.000 description 1
239000007788 liquid Substances 0.000 description 1
229910003002 lithium salt Inorganic materials 0.000 description 1
159000000002 lithium salts Chemical class 0.000 description 1
NCBZRJODKRCREW-UHFFFAOYSA-N m-anisidine Chemical compound COC1=CC=CC(N)=C1 NCBZRJODKRCREW-UHFFFAOYSA-N 0.000 description 1
239000011159 matrix material Substances 0.000 description 1
238000005259 measurement Methods 0.000 description 1
NYGZLYXAPMMJTE-UHFFFAOYSA-M metanil yellow Chemical group [Na+].[O-]S(=O)(=O)C1=CC=CC(N=NC=2C=CC(NC=3C=CC=CC=3)=CC=2)=C1 NYGZLYXAPMMJTE-UHFFFAOYSA-M 0.000 description 1
239000010446 mirabilite Substances 0.000 description 1
239000011259 mixed solution Substances 0.000 description 1
230000004048 modification Effects 0.000 description 1
238000012986 modification Methods 0.000 description 1
239000000178 monomer Substances 0.000 description 1
SFDJOSRHYKHMOK-UHFFFAOYSA-N nitramide Chemical class N[N+]([O-])=O SFDJOSRHYKHMOK-UHFFFAOYSA-N 0.000 description 1
238000005121 nitriding Methods 0.000 description 1
VMPITZXILSNTON-UHFFFAOYSA-N o-anisidine Chemical compound COC1=CC=CC=C1N VMPITZXILSNTON-UHFFFAOYSA-N 0.000 description 1
BMMGVYCKOGBVEV-UHFFFAOYSA-N oxo(oxoceriooxy)cerium Chemical compound [Ce]=O.O=[Ce]=O BMMGVYCKOGBVEV-UHFFFAOYSA-N 0.000 description 1
239000001301 oxygen Substances 0.000 description 1
229910052760 oxygen Inorganic materials 0.000 description 1
230000000149 penetrating effect Effects 0.000 description 1
150000002989 phenols Chemical class 0.000 description 1
239000000049 pigment Substances 0.000 description 1
229920002647 polyamide Polymers 0.000 description 1
229920000515 polycarbonate Polymers 0.000 description 1
239000004417 polycarbonate Substances 0.000 description 1
150000004291 polyenes Chemical class 0.000 description 1
229920001225 polyester resin Polymers 0.000 description 1
239000004645 polyester resin Substances 0.000 description 1
229920005672 polyolefin resin Polymers 0.000 description 1
229920002689 polyvinyl acetate Polymers 0.000 description 1
239000011118 polyvinyl acetate Substances 0.000 description 1
239000004800 polyvinyl chloride Substances 0.000 description 1
229920000915 polyvinyl chloride Polymers 0.000 description 1
XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
230000008569 process Effects 0.000 description 1
KCXFHTAICRTXLI-UHFFFAOYSA-N propane-1-sulfonic acid Chemical compound CCCS(O)(=O)=O KCXFHTAICRTXLI-UHFFFAOYSA-N 0.000 description 1
125000002572 propoxy group Chemical class [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
125000006239 protecting group Chemical group 0.000 description 1
238000000746 purification Methods 0.000 description 1
239000010453 quartz Substances 0.000 description 1
239000002994 raw material Substances 0.000 description 1
WPPDXAHGCGPUPK-UHFFFAOYSA-N red 2 Chemical compound C1=CC=CC=C1C(C1=CC=CC=C11)=C(C=2C=3C4=CC=C5C6=CC=C7C8=C(C=9C=CC=CC=9)C9=CC=CC=C9C(C=9C=CC=CC=9)=C8C8=CC=C(C6=C87)C(C=35)=CC=2)C4=C1C1=CC=CC=C1 WPPDXAHGCGPUPK-UHFFFAOYSA-N 0.000 description 1
238000007670 refining Methods 0.000 description 1
238000007127 saponification reaction Methods 0.000 description 1
239000010980 sapphire Substances 0.000 description 1
229910052594 sapphire Inorganic materials 0.000 description 1
VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
229910052938 sodium sulfate Inorganic materials 0.000 description 1
RSIJVJUOQBWMIM-UHFFFAOYSA-L sodium sulfate decahydrate Chemical compound O.O.O.O.O.O.O.O.O.O.[Na+].[Na+].[O-]S([O-])(=O)=O RSIJVJUOQBWMIM-UHFFFAOYSA-L 0.000 description 1
235000011152 sodium sulphate Nutrition 0.000 description 1
RPACBEVZENYWOL-XFULWGLBSA-M sodium;(2r)-2-[6-(4-chlorophenoxy)hexyl]oxirane-2-carboxylate Chemical compound [Na+].C=1C=C(Cl)C=CC=1OCCCCCC[C@]1(C(=O)[O-])CO1 RPACBEVZENYWOL-XFULWGLBSA-M 0.000 description 1
238000001179 sorption measurement Methods 0.000 description 1
239000011029 spinel Substances 0.000 description 1
229910052596 spinel Inorganic materials 0.000 description 1
238000004544 sputter deposition Methods 0.000 description 1
239000007858 starting material Substances 0.000 description 1
BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
230000002194 synthesizing effect Effects 0.000 description 1
238000010998 test method Methods 0.000 description 1
BFKJFAAPBSQJPD-UHFFFAOYSA-N tetrafluoroethene Chemical group FC(F)=C(F)F BFKJFAAPBSQJPD-UHFFFAOYSA-N 0.000 description 1
WNQPPENQFWLADQ-UHFFFAOYSA-J tetrasodium;4-hydroxy-5-[[4-[[4-[(8-hydroxy-3,6-disulfonatonaphthalen-1-yl)diazenyl]-2-methoxy-5-methylphenyl]carbamoylamino]-5-methoxy-2-methylphenyl]diazenyl]naphthalene-2,7-disulfonate Chemical compound [Na+].[Na+].[Na+].[Na+].[O-]S(=O)(=O)C1=CC(O)=C2C(N=NC3=C(C)C=C(C(=C3)OC)NC(=O)NC3=CC(C)=C(N=NC=4C5=C(O)C=C(C=C5C=C(C=4)S([O-])(=O)=O)S([O-])(=O)=O)C=C3OC)=CC(S([O-])(=O)=O)=CC2=C1 WNQPPENQFWLADQ-UHFFFAOYSA-J 0.000 description 1
OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
LDHQCZJRKDOVOX-UHFFFAOYSA-N trans-crotonic acid Natural products CC=CC(O)=O LDHQCZJRKDOVOX-UHFFFAOYSA-N 0.000 description 1
238000001771 vacuum deposition Methods 0.000 description 1
238000007740 vapor deposition Methods 0.000 description 1
229920002554 vinyl polymer Polymers 0.000 description 1

Classifications

- G—PHYSICS
- G02—OPTICS
- G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
- G02B1/00—Optical elements characterised by the material of which they are made; Optical coatings for optical elements
- G02B1/08—Optical elements characterised by the material of which they are made; Optical coatings for optical elements made of polarising materials
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B31/00—Disazo and polyazo dyes of the type A->B->C, A->B->C->D, or the like, prepared by diazotising and coupling
- C09B31/30—Other polyazo dyes
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
- C09B67/0071—Process features in the making of dyestuff preparations; Dehydrating agents; Dispersing agents; Dustfree compositions
- G—PHYSICS
- G02—OPTICS
- G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
- G02B1/00—Optical elements characterised by the material of which they are made; Optical coatings for optical elements
- G02B1/04—Optical elements characterised by the material of which they are made; Optical coatings for optical elements made of organic materials, e.g. plastics
- G—PHYSICS
- G02—OPTICS
- G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
- G02B1/00—Optical elements characterised by the material of which they are made; Optical coatings for optical elements
- G02B1/10—Optical coatings produced by application to, or surface treatment of, optical elements
- G02B1/14—Protective coatings, e.g. hard coatings
- G—PHYSICS
- G02—OPTICS
- G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
- G02B5/00—Optical elements other than lenses
- G02B5/30—Polarising elements
- G—PHYSICS
- G02—OPTICS
- G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
- G02B5/00—Optical elements other than lenses
- G02B5/30—Polarising elements
- G02B5/3025—Polarisers, i.e. arrangements capable of producing a definite output polarisation state from an unpolarised input state
- G02B5/3033—Polarisers, i.e. arrangements capable of producing a definite output polarisation state from an unpolarised input state in the form of a thin sheet or foil, e.g. Polaroid
- G—PHYSICS
- G02—OPTICS
- G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
- G02B5/00—Optical elements other than lenses
- G02B5/30—Polarising elements
- G02B5/3025—Polarisers, i.e. arrangements capable of producing a definite output polarisation state from an unpolarised input state
- G02B5/3033—Polarisers, i.e. arrangements capable of producing a definite output polarisation state from an unpolarised input state in the form of a thin sheet or foil, e.g. Polaroid
- G02B5/3041—Polarisers, i.e. arrangements capable of producing a definite output polarisation state from an unpolarised input state in the form of a thin sheet or foil, e.g. Polaroid comprising multiple thin layers, e.g. multilayer stacks
- G02B5/305—Polarisers, i.e. arrangements capable of producing a definite output polarisation state from an unpolarised input state in the form of a thin sheet or foil, e.g. Polaroid comprising multiple thin layers, e.g. multilayer stacks including organic materials, e.g. polymeric layers
- G—PHYSICS
- G02—OPTICS
- G02F—OPTICAL DEVICES OR ARRANGEMENTS FOR THE CONTROL OF LIGHT BY MODIFICATION OF THE OPTICAL PROPERTIES OF THE MEDIA OF THE ELEMENTS INVOLVED THEREIN; NON-LINEAR OPTICS; FREQUENCY-CHANGING OF LIGHT; OPTICAL LOGIC ELEMENTS; OPTICAL ANALOGUE/DIGITAL CONVERTERS
- G02F1/00—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics
- G02F1/01—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour
- G02F1/13—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour based on liquid crystals, e.g. single liquid crystal display cells
- G02F1/133—Constructional arrangements; Operation of liquid crystal cells; Circuit arrangements
- G02F1/1333—Constructional arrangements; Manufacturing methods
- G02F1/1335—Structural association of cells with optical devices, e.g. polarisers or reflectors
- B—PERFORMING OPERATIONS; TRANSPORTING
- B32—LAYERED PRODUCTS
- B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
- B32B2457/00—Electrical equipment
- B32B2457/20—Displays, e.g. liquid crystal displays, plasma displays
- B32B2457/202—LCD, i.e. liquid crystal displays
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2323/00—Functional layers of liquid crystal optical display excluding electroactive liquid crystal layer characterised by chemical composition
- C09K2323/03—Viewing layer characterised by chemical composition
- C09K2323/031—Polarizer or dye

Landscapes

Physics & Mathematics (AREA)
General Physics & Mathematics (AREA)
Optics & Photonics (AREA)
Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Nonlinear Science (AREA)
Chemical Kinetics & Catalysis (AREA)
Mathematical Physics (AREA)
Crystallography & Structural Chemistry (AREA)
Polarising Elements (AREA)
Health & Medical Sciences (AREA)
Medicinal Chemistry (AREA)
Polymers & Plastics (AREA)

TW101103856A 2011-02-07 2012-02-07 偶氮化合物、染料系偏光膜及偏光板 TWI509030B (zh)

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JP2011023747		2011-02-07

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TW201241096A TW201241096A (en)	2012-10-16
TWI509030B true TWI509030B (zh)	2015-11-21

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US (3)	US9244198B2 (fr)
EP (1)	EP2674461B1 (fr)
JP (1)	JP5899122B2 (fr)
KR (1)	KR101932467B1 (fr)
CN (1)	CN103347959B (fr)
TW (1)	TWI509030B (fr)
WO (1)	WO2012108169A1 (fr)

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JP5899122B2 (ja)	2011-02-07	2016-04-06	日本化薬株式会社	アゾ化合物、染料系偏光膜及び偏光板
TWI560244B (en) *	2011-07-08	2016-12-01	Nippon Kayaku Kk	Polarizer and polarizing plate
US20140218797A1 (en) *	2011-09-09	2014-08-07	Polatechno Co., Ltd.	Polarizing Element And Polarizing Plate
EP2990842A4 (fr) *	2013-04-03	2016-11-23	Nippon Kayaku Kk	Élément polarisant à base de colorant achromatique, et plaque de polarisation
WO2014162633A1 (fr) *	2013-04-03	2014-10-09	日本化薬株式会社	Élément polarisant achromatique, et plaque de polarisation
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HK1226428B (zh) *	2014-03-31	2017-09-29	日本化药株式会社	偶氮化合物及含有该化合物的染料型偏振膜和偏振板
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WO2017135392A1 (fr) *	2016-02-04	2017-08-10	日本化薬株式会社	Composé azoïque, élément polarisant et plaque polarisante utilisant celui-ci et dispositif d'affichage
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JP6788461B2 (ja) *	2016-09-29	2020-11-25	日本化薬株式会社	偏光素子、偏光板及び液晶表示装置
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- 2012-02-06 US US13/980,184 patent/US9244198B2/en not_active Expired - Fee Related
- 2012-02-06 WO PCT/JP2012/000775 patent/WO2012108169A1/fr not_active Ceased
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- 2012-02-06 CN CN201280008020.2A patent/CN103347959B/zh active Active
- 2012-02-06 KR KR1020137018071A patent/KR101932467B1/ko active Active
- 2012-02-07 TW TW101103856A patent/TWI509030B/zh active
2015
- 2015-07-30 US US14/813,163 patent/US9341746B2/en not_active Expired - Fee Related
- 2015-12-15 US US14/969,517 patent/US20160109619A1/en not_active Abandoned

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Also Published As

Publication number	Publication date
TW201241096A (en)	2012-10-16
JPWO2012108169A1 (ja)	2014-07-03
EP2674461A1 (fr)	2013-12-18
JP5899122B2 (ja)	2016-04-06
KR101932467B1 (ko)	2018-12-26
CN103347959A (zh)	2013-10-09
CN103347959B (zh)	2016-01-20
KR20140019309A (ko)	2014-02-14
HK1187940A1 (zh)	2014-04-17
US9244198B2 (en)	2016-01-26
US20150331148A1 (en)	2015-11-19
EP2674461A4 (fr)	2016-02-10
US9341746B2 (en)	2016-05-17
US20160109619A1 (en)	2016-04-21
EP2674461B1 (fr)	2019-03-27
US20130302538A1 (en)	2013-11-14
WO2012108169A1 (fr)	2012-08-16

Publication	Publication Date	Title
TWI509030B (zh)	2015-11-21	偶氮化合物、染料系偏光膜及偏光板
TWI503377B (zh)	2015-10-11	偶氮化合物及其鹽，含該等之染料系偏光膜以及偏光板
TWI565761B (zh)	2017-01-11	偶氮化合物及含該等之染料系偏光膜及偏光板
JP5366947B2 (ja)	2013-12-11	アゾ化合物及びその塩、並びにそれらを含有する染料系偏光膜並びに偏光板
TWI406908B (zh)	2013-09-01	偶氮化合物及含其之染料系偏光膜
TWI399410B (zh)	2013-06-21	偶氮化合物及其鹽以及含該等之染料系偏光膜
CN103224713B (zh)	2015-03-18	偶氮化合物和含有该偶氮化合物的染料偏振膜
JP6736549B2 (ja)	2020-08-05	アゾ化合物及びそれらを含有する染料系偏光膜並びに偏光板
KR102581552B1 (ko)	2023-09-21	아조 화합물 및 그것들을 함유하는 염료계 편광막 그리고 편광판
HK1187940B (en)	2016-08-26	Azo compound, dye-based polarizing film, and polarizing plate
HK1187939B (en)	2015-06-26	Azo compound, salt thereof, and dye-based polarizing film and polarizing plate containing same
HK1133028B (en)	2014-02-28	Azo compound and dye polarizing film containing the same
HK1133028A (en)	2010-03-12	Azo compound and dye polarizing film containing the same
HK1187941B (en)	2015-09-11	Azo compound and dye polarizing film containing the same
HK1183682B (en)	2015-06-26	Azo compound and salts thereof, as well as dye-based polarization films and polarizing plates comprising the same
HK1153217B (en)	2014-05-30	Azo compound and salts thereof, as well as dye-based polarization films and polarizing plates comprising the same